


Betting Against Dean Gets You Screwed

by Enamourous



Category: Supernatural
Genre: M/M, panty!kink
Language: English
Status: Completed
Published: 2013-04-01
Updated: 2013-04-01
Packaged: 2017-12-07 03:44:52
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 2,693
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/743817
Author URL: https://archiveofourown.org/users/Enamourous/pseuds/Enamourous
Summary: <blockquote class="userstuff">
              <p>Sam loses a bet against Dean, so Dean makes him wear women's underwear.</p>
            </blockquote>





	Betting Against Dean Gets You Screwed

By lunchtime Sam has stopped blushing.

It’s only after he tells himself about million times that no one knows he’s wearing them, that he’s able to keep the pink from spreading through his cheeks every time anyone looks at him too closely. They don’t know. There’s no way they’d know. The only one who knows is Dean, and thank god they don’t have any classes together. 

 

So yeah, Sam’s been able to handle this pretty well considering. But of course Dean isn’t making it easy. He goes out of his way to pass Sam in the hall and when that happens Sam can’t manage to keep a blush from blossoming through his face. Because Dean knows that he’s wearing them, and he knows that it’s mortifying. But that’s why it’s fun after all. And Sam should have known better than to bet against him. Betting against Dean just gets you screwed.

This time Sam’s punishment for thinking he could win a bet against his brother is a pair of emerald green lace panties that Dean helpfully provided, that had to be worn all day or until Dean told him he could take them off. Sam doubted Dean would let him take them off early, he knew his brother just liked to add that onto the bargain. To give Sam the chance to beg him.

And by the time the last period bell rings Sam’s not too far away from sinking to that level. The only reason he doesn’t is because when he sees Dean’s smug grin when he gets out to the parking lot, there’s no way he’s going to give him the satisfaction.

“Hey Sammy,” he says, leaning up against the side of the Impala like he’s hotter than the Louisiana sun. He kind of is, but that’s not the point.

“Hey.”

“How was your day?” He asks with a cocky grin.

Sam walks by him and around the front of the car so he can try the passenger side door. It’s locked.

“Oh fuck off Dean. And let me in.”

His brother chuckles and slides in the front seat so he can lean over and unlock Sam’s door. When he gets in he doesn’t look over at Dean, hoping he’ll keep his mouth shut and not subject him to a car ride full of panty jokes but that would be wishful thinking.

“Got your panties in a twist eh little brother?” Dean asks innocently.

Aaand there it is.

Sam does his best not to play into it, he knows Dean’s trying to get him flustered but he’s not going to let him.

“Yeah actually,” Sam says, shifting uncomfortably. “I don’t know how anyone wears these things.”

“Well girls have a lot less merchandise to shove in there for one.” Sam ignores Dean’s reference to his junk.

“Well they’re scratchy,” Sam huffs.

“Dude just be happy those are the ones I picked for you. I coulda put you in a thong.”

Sam rolls his eyes at that. “Not like you didn’t want to,” He mumbles under his breath.

“What?” Dean says.

“Nothing.”

Dean, by some miracle, doesn’t push it and instead starts the car, bringing the engine to life in a familiar purr that Sam can feel rumbling through him. When they get onto the road Dean breaks the silence again.

“So how was it?”

“How was what?”

“Did anyone see them?”

Sam doesn’t think that question justifies an answer so he doesn’t give it one. “Jesus Dean you’re so weird,” he says instead, rolling his eyes and slumping down in the seat.

“Hey man, you’re the one with his junk covered in lace,” Dean answers, turning his head to give Sam a once over that makes him feel painfully exposed.

“No thanks to you.”

“You are still wearing them aren’t you?” Dean asks suddenly, giving Sam a suspicious glance.

“Yes,” Sam says annoyed.

“Show me.”

“Deaan,”

“C’mon,” Dean says with a snap of his fingers, gesturing for Sam to pull up his shirt a little. “I gotta know you’re not skimping on your word.”

Sam sighs again and shifts in his seat, pulling his shirt up a bit and slipping a finger under the waist of his jeans so he can push them down to reveal a sliver of the green lace stretched over his hipbone. Dean’s eyes flick down to the stripe of color and he makes a contented noise.

“Satisfied?” Sam says, his embarrassment and agitation audible in his tone.

“Yeah,” Dean says, looking at the road. Sam watches as the corner of his mouth pulls up into a small grin. “You want to take them off don’t you?”

“No Dean, I love wearing them so much I’m just never going to take them off ever.”

“Well whatever floats your boat kiddo,” Dean says. Sam just shoots him a look that could kill.

“You don’t have to wear them anymore,” Dean says after a few moments of silence, and Sam takes his gaze from the field rushing by outside to give his brother a wary look. Sure enough, there’s something in Dean’s expression that tells him he’s not giving him a get out of jail free card.

“Okay..,” Sam says, waiting for the catch.

“Okay what? I mean, you can keep ‘em on if you want I’m not stopping you.”

“I don’t want to keep them on,” Sam says quickly.

“Only on one condition though,” Dean says slowly, and Sam’s stomach sinks. He knew something else was coming. “You gotta let me take them off.”

“What? No!”

“Well, you’re just gonna have to wear them the rest of the day then.”

“You’re such a jerk.”

“It’s your own fault if you want to leave them on bitch,” Dean says smirking and thrumming his fingers on the steering wheel to the sound of the radio. “Maybe I’ll tell Dad you’re wearing them,” he says and grins even more.

“You wouldn’t.”

“I so would.”

And Sam’s not sure he could cope with the idea of that. Dad already thinks he’s the weird one in the family, he doesn’t need to add this to the list of strokes against him. He can already see their dad’s face when Dean tells him, and that’s enough to make him want to throw up.

“Fine,” Sam mutters out.

“Hm?”

“I said okay fine,” he says again louder, arms crossed.

“You sure dude? I don’t want to spoil your fun.”

Sam just glares and Dean throws his hand up in mock defense. “Alright alright,” he says, turning down a dusty side road. “Just making sure.”

Dean parks the car on the side of the road and Sam is grateful for once that they’re in the middle of nowhere. A stranger seeing his brother pulling lace underwear off of him on the roadside is something he doesn’t want to add to the list of reasons his life is the worst ever.

“Alright Sammy, backseat.”

He does as he’s told, mostly because he wants this whole thing to be over with and Dean’s having far too much fun for this to be bearable anymore.

He opens the back door and sits on the edge of the seat, letting his legs hang out of the car, and looks over his shoulder to see Dean walking around to meet him. He looks up miserably once Dean’s standing in front of him. And Dean laughs quietly.

“Aw c’mon it can’t be that bad,” his voice softer than it had been before.

Sam shrugs. He’s being childish by letting this get to him so bad but he hasn’t had a great week alright? And Dean’s been milking this one for all it’s worth.

“Okay, jeans off.”

He unbuttons his jeans and shimmies out of them, pulling his ankles through and pushing them over into a heap in the gravel by his feet. Dean’s seen him naked before a billion times. But something about wearing these stupid panties makes him feel more naked than if he wasn’t wearing anything at all. Not like this is much better anyway, they’re see-through enough it’s like they’re barely there. Plus Dean is taking his time just letting the sight soak in, so Sam doesn’t even try to stop the heat from flushing through his cheeks this time.

After what seems like ages to him, Sam’s annoyance pushes through his embarrassment. “Are you gonna take them off or just stare at me all day?”

“Damn you’re pissy,” Dean says, but he walks closer. “You shouldn’t be. They look good on you.”

“Shut up.”

“No I mean it,” He says, moving even closer and dropping to his knees in the gravel in front of Sam’s legs. “Better than any girl.”

And the way he says it goes straight to Sam’s dick and he hates himself for it because dammit Dean has been pissing him off all day and he wasn’t going to be this easy this time.

But Dean puts a warm hand on his knee and pushes it up over his thigh until he reaches where the lace is straining over Sam’s dick and then he massages his hand over that too and Sam knows then that he isn’t going to argue.

“They’re not all bad are they?” Dean asks, smoothing a hand over the skin on Sam’s hip, inching fingers under his t-shirt and pushing his palm over the bottom of Sam’s ribs.

“They kind of are.”

“But Jesus Sam, you look hot in them,” Dean says, nudging Sam’s knees open wider with his body when he leans forward to wrap an arm around Sam’s back and pull him forward so he can kiss his hips. “I’ve been thinking about you all day.”

Sam pushes his fingers gently through Dean’s hair, and lets him continue.

“Knew you’d let me take them off,” He says, mouthing over the lace on his hipbone, closer and closer, letting his warm breath seep through the fabric. Sam is definitely hard now. When he looks down to see his erection straining at the panties, pulling them tighter than they already were, there’s a moment where he thinks he might understand why Dean likes this. It’s dirty.

“I knew you’d let me make it up to you,” He continues, pressing his lips to Sam’s cock through the lace and bringing a hand to rub a little lower over his balls. And somehow what was scratchy and uncomfortable earlier is freaking heavenly now, and Sam leans into Dean’s hand in an attempt to get more friction. He’s always been so damn responsive to Dean’s touch and he’s already dampening the fabric that’s stretched over the head of his dick. It’s a deeper green where it’s wet from Dean’s spit and Sam’s precome and the afternoon light is catching the moisture, making it glisten.

Sam pushes his hips forward a little and Dean slides his hands under Sam’s ass so he can hook his fingers into the waistband of the underwear in the back and pull them down to the top of Sam’s thighs.

Sam’s hard enough that his dick rests heavy against his belly while he leans back so Dean can finally pull the damn things off for easier access. The second they’re off he feels better and even though this means he’ll have to go commando the rest of the way home, he doesn’t even care. Actually, he doesn’t really care about anything when Dean’s mouth is back on him again, sucking at his balls and licking up the underside of his dick. Sam lets his legs fall apart even further, and Dean inches his body closer so he can lean an arm on the seat next to Sam’s ass while he works his mouth over his little brother.

Dean’s done this enough times that he knows how to get Sam off in seconds but he never does. He always takes his time and lets Sam enjoy it. It’s partly because it makes Sam happy, but it’s also because Dean’s favorite sounds in the world are the ones Sam makes when Dean’s working him over like this. The sounds only he has ever been able to pull from his brother.

So he goes slow, paying attention to every move Sam makes, every hitch of breath. He reads him close and gives Sam exactly what he needs. And Jesus Christ, he just wants to push Sam back onto the leather and fuck him but he’s not going to, because Sam put up with his shit all day. Dean’s going to give him this.

Eventually Sam is moaning softly, eyes closed and head lolling back, and Dean puts a hand on his belly to push him gently back onto the seat. He gets a knee on the floor of the Impala so he can get a better angle and pushes Sam’s legs up so one is thrown over Dean’s shoulder and the other is bent, foot gripping on the edge of the seat. Sam’s stopped being embarrassed at this point, his legs are shamelessly spread and he’s completely on display for his brother but he doesn’t care because Dean’s making it feel so good and he knows what’s coming next because this is his favorite and he wants it so bad he’s got to stop himself from grabbing Dean’s hand and pushing his fingers inside when he feels a fingertip brush his entrance.

Sam holds onto Dean’s wrist but he lets him set the pace because even though Dean’s choosing to do this, it’s still his rules. He pushes in slow at first and lets Sam’s body adjust to just one spit slicked finger. It’s not always comfortable in the beginning but it gets to be soon enough, while Dean patiently works him open nice and slow. Letting the pleasure in Sam’s body work up gradually, spreading through him like warm water.

Dean pushes Sam’s shirt further up his torso so he can watch his stomach rising in shallow breaths while he fingers him. He starts to massage his dick again too, because he can tell Sam’s getting closer now and he’s getting impatient to see his little brother come.

“Fuck, you’re so beautiful like this Sam,” He says quietly, and Sam’s muscles tense in his abdomen as Dean continues to stroke him. His skin looks impossibly soft in the warm evening light. “Wish I could touch you all the time.”

“Dean,” Sam says faintly, letting the name slip out of his lips in something barely above a whisper. And Dean rests the side of his forehead on Sam’s thigh. He’s so fucking hard in his own pants right now it hurts.

Sam’s about to come, he can feel it. He tightens his grip on Dean’s wrist and holds his breath in his lungs, arching when Dean senses that Sam’s almost there and starts fingering him faster, crooking his fingers slightly to rub Sam just right.

And this might be selfish of Dean but he wants to kiss his brother so bad he might just die so he lets go of Sam’s cock and slides an arm under his back so he can pull him up, careful to keep the rhythm of his fingers going, careful to keep hitting Sam’s prostate.

Dean pulling him up shoves his fingers inside deeper inside of his brother and Sam gasps, before his breath is swallowed up by Dean’s kisses. When he brings a hand back to stroke him off a few more times Sam comes hard, moaning against Dean’s lips and gripping his shoulder tight.

His come is all over Dean’s hand and shirt when they break apart and Sam’s about to apologize but Dean leans down and sucks off the come that’s dripping down his dick and that stops his apologies in their tracks. When his brother straightens up again Sam can see some of it on his shining on his brother’s lips and for some reason it makes him smile.

“Okay maybe they aren’t all that bad,” Sam says, a little shakily. And Dean ruffles the hair on the side of his head.

“Yeah I thought you might change your mind.”

“You’re gonna wear them next time though,” Sam says, and Dean laughs. 

“Wanna bet?”


End file.
